Date: Fri, 22 Jul 2005 05:47:06 -0700 (PDT)
From: Gabrielle Wolfe <gabbytv509@yahoo.com>
Subject: Hilton Hottie (TG story)

Hilton Hottie
by Gabrielle Wolfe 2005
gabbytv509@yahoo.com

The Room

I checked into the Hilton in Seattle and then went up to my room. While it
wasn't the best room i've ever stayed in it was one of the best
experiences. I unpacked my bags and then picked out the outfit I'd planned
on wearing. I'd been planning this night for awhile and so had a good idea
of the "look" I wanted. After I set the outfit aside I hopped in the shower
to get the stale plane air out of my nostrils and to do a last minute shave
to get myself extra smooth. Stepping out of the shower I quickly blotted my
skin dry and then blew dry my hair. In a step out of the ordinary for me I
stopped by my friend Katie's shop in NW Portland and had extensions put in
for the weekend. While it's a bit expensive to do it is nice to have
someone you know and trust with your "beauty secrets". Usually I only have
shortish hair but for the weekend I had hair halfway down my back and it
was quite curly to boot.  After my hair was dry I softly ran a brush
through it until it was tangle free and had just the right amount of animal
sexiness.

Now that my hair was taken care of let's get dressed I thought. Stepping
over to the bed I picked up the centerpiece of my outfit. A black patent
leather thong that I recieved three days earlier from one of my online male
friends along with the confirmation for my hotel room in Seattle. Smiling
as I set it aside again I picked up a pair of thigh high stockings and
slowly rolled them up my perfectly smooth legs. Once they were pulled tight
I slipped on my favorite black garter belt and then clipped the stays into
place. Next I pulled the leather thong on and tucked my cock back between
my legs before pulling the thong all the way on. Looking in the mirror I
couldn't see a hint of my cock or my balls. Excellent I thought.

Once that was done I opened the small black box in my overnight bag and
took out the adhesive and my DD breast forms. I applied a bit of the
adhesive to the back of the forms and then pressed them against my chest
firmly and waited for the adhesive to dry. One of my on again off again
lovers works in special effects and had hand made these perfectly for
me. The skin tone was perfect and when applied had almost no seam between
my skin and the forms. The look perfect when I wear them.  Next I grabbed
my cupless full boned corset (girls if you don't have one with front clasps
and a zipper you gotta get one. They are so much easier to put on) and with
a quick exhalation of air zipped and clasped it up. Then taking as deep a
breath as I could I went bent down and picked up my black patent
skirt. Pulling it up past my girlish hips and ass I felt the leather caress
my perfectly smooth bare ass and shivered knowing I'd have something other
than a skirt caressing it soon.

Next I headed over to the makeup table and began applying my makeup. I knew
that to match that thong I'd need to go with something a little on the
vampy side so after a quick application of foundation I gave myself a light
coat of "whorepaint". First I applied some deep red rouge and then put on
some dark grey eyeshadow and also outlined my eyes with eyeliner before
adding a thick coat of mascara. Then I searched my makeup bag until I found
my deepest cocksucking red lipstick and applied it. Finally I gave my lips
that lickable shine with a bit of lip gloss.

Once my makeup was done I slipped on a simple lightweight blouse buttoned
to just above my nipples added the very last bit to my outfit, a simple
silver chain with a pendant that read "toy". With a quick glance in the
mirror I knew that anyone who saw me would know I was on the prowl hunting
for just one thing.  checking to make sure that everything was in place and
that I didn't have anything remotely male about me I slipped on my come
fuck me pumps and grabbed my purse before heading out the door.

The Bar.

As I sashayed up to the elevator the doors opened and out came a guy in a
suit carrying his bags. As his eyes travelled over my body they lingered on
my necklace and I noticed him flush. As I passed him my hand reached out
and caressed his crotch as I purred "hi baby" with a sly smile on my
face. Continuing past him I slipped into the elevator and pressed the
button to reach the hotel bar.  After a short time the doors opened and I
strode out of the elevator and headed for the bar. I noticed quite of the
guys in the lobby look my way as my ass and tits jiggled in their
midst. Entering the totally empty bar I took a moment to let my eyes adjust
before moving. Spotting a table in a corner I sat down and crossed my legs
while fishing in my purse for a cigarette. I'd just taken my first drag
when the waitress came to my table.

I ordered a midori sour and looked around to see if my friend was there
yet. Not seeing him I continued to look around seeing if I could find a
weary businessman to flirt with. I noticed over at the bar a youngish guy
furtively checking me out. I took a drag on my cigarette while staring his
direction and then languidly licked my lips before exhaling. As the
waitress went past him to make my drink he turned and said something to
her. I smiled knowing he was using the oldest pickup in the book. As the
waitress nodded her assent she continued making my drink and then came over
and delivered it to me. She told me the gentleman at the bar had already
paid for my drink. I told her to let him know I really appreciated it and
to send him over so I could thank him personally. She said no problem with
a smile and then headed back to the bar. As she told him my message he
smiled and then picked up his beer (guinness from the color) and came
over. He introduced himself as Chris and asked if I minded if he sat
down. I told him I'd love it if he did.

One thing I've noticed is travelling businessman never turn down the
attention of an attractive lady. I could feel his blue eyes lingering on my
cleavage as he sat down. Thanks to the excellent construction of my breast
forms and the dim lighting in the bar I knew that all he saw was a 100%
natural woman.

Chris told me that he had recently applied himself 100% to work due to a
recent breakup. Typically when I hear this sort of story I usually try to
make a break for it as quickly as possible. But hearing the emotion in his
voice I could tell that he was still completely in love with this girl. I
asked him how long they'd been together and he told me 6 years. Hmm someone
who isn't totally commitment phobic and in love? Well this could be a nice
challenge. Chris went on to tell me that he didn't expect anything other
than some conversation since I was the first person he'd seen walk into the
bar in the 3 hours he'd been sitting there. He gave me a wry grin and said
that didn't sound like the greatest way to describe himself. I smiled back
and asked him what he did.

He explained that he was a network engineer in town to work on a project
for a few weeks. Usually I'd either have gone home to the girlfriend for
the weekend or brought her up. Faced with returning to an empty house full
of memories I decided the hotel would be a better place.

I placed my hand on his and told him I fully understood what he was going
through. I let him in on the secret (well not THE secret' that could come
later) of how I became such an enticing creature. My old ex had really done
a number on me and brought out the sexy vibrant woman he now saw. Before I
was hurt so badly I wasn't nearly as outgoing nor did I take such great
pains to make myself look so attractive.

He smiled that same sexy wry grin again and told me he doubted I could ever
look unattractive. As my hand rested upon his I noticed how long his
fingers were. His hands were quite strong looking too. I noticed also that
his shirt sleeves were rolled up revealing deeply tanned muscular
forearms. (is it getting hot in here or is it me?)  placing his other hand
on top of mine he smiled a quiet smile and told me that whatever hurt I'd
suffered it seems to have made me the better for it. When his hand covered
mine I could suddenly feel where the heat was coming from. This guy was
basically a human heat pump. mmm warmth like that means that he'd heat me
up from the inside out. Decision made. I'd seduce this guy and have him
begging to fuck me. Maybe even convince him to try sucking a tranny cock.

The Seduction

As we'd been talking I'd noticed a band setting up in the corner of the
bar. They'd completed their setup and had just started playing one of my
favorite songs "Sentimental Journey". I smiled and said that I loved
dancing to this song as I grabbed Chris' hand and dragged him towards the
dance floor. He resisted at first but when I leaned in close to him and
started slow dancing I could tell how much he needed a woman's closeness. I
kept my distance at first and then slowly closed in until I had most of my
body millimeters away from his. I put my face in towards his neck and
slowly breathed warm air along his throat. As I did this I felt him tense
slightly and then felt a nice large pressure against my thigh (oh my..this
is turning out to be an excellent night). As we continued to dance I felt
him press more of his crotch against me. Slowly turning I wrapped his arms
around me and pressed my bottom against his crotch and let him slowly grind
his hard cock against my ass. When the song ended shortly thereafter I
turned and gave him a quick kiss and asked if he would excuse me for a
moment, "powder room".  He blushed a bit as he realized what we'd been
doing on the dance floor and then nodded a yes.

I stopped by the table and grabbed my purse before heading to the ladies
room. Once inside the ladies room I checked to make sure that no taletell
bulge showed in my skirt (this guy had the natural right moves to turn a
girl on!). Once I'd checked my skirt I checked my makeup and then pulled
out my cellphone to call my friend who was supposed to meet me later. When
he answered I told him I'd found a deserving lonely guy who needed some
attention. He laughed and said he'd talk to me in the morning.

I put my phone away and then with a last check in the mirror headed back
out to Chris.  I sat down and slowly and languidly sucked at my drink with
my red full lips wrapped around the straw as my eyes stared directly at
Chris' crotch. He swallowed a few times and asked if I wanted anything else
to drink.  (ah ha! someone else who likes double entendre).  I told him I
would rather go someplace else for something to eat.

He smiled when I said that and mentioned that he knew a nice cozy place
where both of us could get something to eat and that it might even fill me
up.  I laughed and said that I hoped so since I was absolutely starving and
really wanted to feel full.  (Granted it wasn't the wittiest but since we
were both horny and had all of our blood below our waists it was great!).

Chris stood up and pulled out my chair and then held out his hand. I took
his hand and then leaned in close as I felt his hand move in towards my
lower back and then felt his fingers gently stroke the middle of my ass
(just an inch or so above my anus...so few men know how sensitive that area
is) I shuddered a little and leaned in closer to him as we walked out the
door.

We reached the elevator and I noticed in the brighter light Chris was
looking at me with a thoughtful look on his face. Inwardly I wondered if he
had "read" me. As the doors opened we stepped in and he pressed the button
for the 9th floor. No sooner had the door closed when I felt his fingers
turning my head towards his and then his lips touched mine. Within seconds
my ass was being kneaded under his strong fingers and my mouth was being
probed by his strong tongue. I reached my hand down to his crotch and gave
him a nice squeeze. Only a few more moments and I'd have that monster in my
mouth.

The elevator came to a stop and we quickly composed ourselves before the
doors opened. As they opened we both strode purposefully for his room (he
in the lead since he knew where it was and I didn't). He put his key in the
door and opened it in one fluid motion.

Within seconds we were in each others arms again groping and licking and
biting and kissing. As he started to put his hand under my skirt I stopped
him by kneeling down and beginning to unbuckle his belt. I ripped his belt
off and then unbuttoned and pulled off his pants. Then looking up into his
eyes I pulled his zipper down with my teeth and then reached into his
underwear and pulled out a nice 7.5" thick cock. It was perfect in it's
dimensions and was accompanied by a very large pair of nuts. I licked up
the shaft from the base and then wrapped my lips around the head just like
I had that straw earlier. Slowly I slid down his length until I'd buried my
nose in his dark pubic hair. I placed my hands against his firm ass and
continued bobbing my head up and down on his throbbing cock while taking
his boxers off the rest of the way.

After I sucked him for a few minutes I took my mouth off and blew cool air
across his swollen balls as I stroked his full length with my hand. He
groaned as I took one ball and then the other into my mouth and rolled them
gently around on my tongue. After doing this for a bit I turned my
attention back to his huge cock. As I continued to stroke and suck him (my
tongue tracing little circles around his shaft) I felt him starting to get
close to cumming.

Stopping my attentions on his cock I instead turned to that delectable
morsel of flesh on his ass and began slowly and sensuously licking at his
ass while continuing to slowly stroke him. Once his ass was fully wet by my
saliva I returned to my oral attentions of his incredibly hot and tasty
cock. While I felt him tense from my ministrations I slowly slipped my
middle finger into his surprisingly relaxed asshole and then began
fingerfucking him in sequence with the bobbing of my head. A few minutes of
this and he started twitching before suddenly yelling that he was about to
come.  I pulled his cock out of my mouth with a nice satisfying pop and
then kept stroking his lipstick and saliva coated cock until he exploded
all over my face and tongue. I lapped at the massive torrent of hot jism
spattering me until he finally collapsed back on the bed. Not wanting to
miss a drop of his tasty cum I slowly and languidly licked up every drop I
could while still milking the last bits out of his semihard cock.

Returning the favor

Once I was finished I crawled up on the bed beside him and looked into his
eyes. He gave me a weak smile and asked if he could return the favor in
some way. I smiled back and said I'd be thrilled if he would. I then leaned
over and gave him a deep kiss letting our tongues dance. Surprisingly I
soon felt him start to grow hard again as well as noticed that he was
softly stroking my cock through my leather thong.

I sat up and looked at him for any signs of freaking out but relaxed when
he said that I was bigger than he thought a ts would be. He smiled when he
watched my expressions change from scared to shocked. I told him that I
wasn't actually a TS but only a parttime TV. He said that he hadn't ever
met a TV that was not only passable but so gorgeous. I laughed and told him
that he was just trying to take advantage of me.

With that same wry grin he looked down and pulled aside my thong and then
with a quick movement took my entire 8 inches into his mouth. I gasped as
his tongue circled the head as he slid down along the shaft until I could
feel his tonsils pushing against my swollen head. I lifted my skirt up a
bit more so I could watch this cute guy sucking my cock with such
joy. After a few minutes of sucking he lifted my ass up so he could pull my
thong off completely leaving my ass in his thick hot hands. As he sucked he
slowly started fingering my ass and then used his other hand to stroke and
fondle my smooth shaved balls.

I pulled him off my cock and then gently tugged him up to me until our
stiff cocks were rubbing together and continued kissing him. As we lay back
on the bed I felt his hands grab ahold of my ass and then he slid me over
his body until I was laying on top of him. I reached down and adjusted our
cocks so that they were side by side and began stroking them both while our
tongues continued to dance together. I felt his hips slide forward as we
both began to twitch in pleasure. His lips left mine and I felt his teeth
nibble at my neck and shivered as he bit my pleasure zones perfectly. I
pulled his shirt up to feel his chest muscles and then with his help
stripped his shirt completely off. Licking his chest and nipples and then
kissing down to his cock I gave it a few licks and sucks while pulling on
his balls a bit more.

Sitting up a bit I grabbed a condom out of my purse and slowly unrolled it
down his cock using my tongue (a girl can never know enough tricks) and
then leaning forward I guided him into my hot waiting ass. As I felt his
hot cock fill me completely I knew I was right when I'd felt the heat
coming off of him in the bar. I felt his throbbing heat sear through my
loins as he slowly lifted himself into me in perfect rhythm. After a few
minutes of riding his cock he grabbed me with his powerful arms and then
flipped me over so he was kneeling over me. Then he started fucking me
deeper and harder as my groans of pleasure began to mount. Then With
another quick adjustment I saw him standing on the floor while continuing
to relentlessly pounding away at my ass.

He leaned down and took my rockhard cock into his mouth and began a
rhythmic cycle of sucking and thrusting that had me convulsing in spasms of
extacy. Within 2 minutes I knew I was going to cum and then with a squeal I
felt my body shudder as wave after wave of orgasm flowed through me. As I
filled his mouth with my seed I felt his cock begin to swell and then felt
the wonderous spurts of his cum spurting into my ass. The twitching of his
cock was enough to give me a second orgasm and a smile of genuine pleasure
on both our faces.

I felt Chris collapse against me and then looked into his eyes as we kissed
and exchanged some of my cum that he'd held in my mouth. The texture of his
silky lips and tantalizing tongue mingled with the sticky sweetness of my
cum. We lay there for a few minutes until he sat up and grabbed a pack of
cigarettes out of his pocket and offered me one. I accepted gratefully and
we lay back down and smoked. I asked him how long he'd been into Tgirls and
he told me a few years. I asked if he dressed and he told me no. He asked
how long I'd been dressing and I told him about how I'd watched a tranny
film in an adult bookstore years before and found that I really wanted to
be the guy in drag sucking off other guys.

As I described my "origins" I felt myself growing hard again and so I
finished my cigarette and began stroking us both. He told me that it was
still my turn so I asked if he minded if I tried that wonderous trick he'd
used on me. He told me that he'd love me to. I lifted his legs and began
eating his tight ass making sure to get it nicely relaxed and wet. Once I
felt his body shake with pleasure I grabbed another condom out of my purse
and slipped it onto my cock. Slowly and gently I slid my cock into his hot
ass and began sliding in and out carefully making sure not to cause him any
pain. Once I'd felt him relax enough I leaned down and kissed and nibbled
at his lips before I started pounding away. After a few minutes I leaned
down and took his cock into my mouth. The pattern of sucking and then
thrusting took me a few moments to get the hang of but eventually I got it
and started increasing my speed until I was pistoning in and out of him as
fast as I could.

After 10 minutes of this I felt his cock start to twitch and swell and then
felt another torrent of cum spatter inside my mouth. Swallowing as much as
I could I sat up fully and stroked his cock as fast as I was pumping away
at his ass smiling as spurt after spurt of his cum hit me in the chest
(damn did his cock have some power!) I pointed the head at his chest and
directed the last 3 jets of cum onto it. I felt myself starting to cum as
well by this point and so feeling a bit overly randy pulled out of his ass,
yanked off the condom and came all over his face tongue and chest. He
leaned forward as I did it and then wrapped his lips around my cock to get
the last few drops of cum out of it with a few gentle sucks.

I leaned down against him and licked the cum off of his face and chest. He
turned around into a semi 69 position and licked me clean as well. Once we
were both relatively cleaned up of cum we went back to kissing gently until
we fell asleep with our legs intertwined.

Epilogue

I woke up with the sun shining in the window and Chris nowhere to be
found. I heard the shower running so I slipped off my stockings, blouse,
skirt and corset off and padded into the bathroom. His back was to me so I
had a perfect view through the glass shower door to his tight tanned
ass. It was enough to give me a nice solid morning erection. Silently I
opened the door and then stepped into the shower. Closing the door I
pressed my cock and breasts against him and then wrapped my arms around
him. I gave him a quick kiss on the neck and then he turned around and
pressed his cock against mine. Within moments we were kissing and stroking
each other again and shortly thereafter I felt the throbbing heat of his
soapcovered cock sliding into my still sore ass. He held me up with his
arms and thrust away until with a mighty grunt I felt his sticky seed
coating my insides. Once he'd finished dropping a load I pushed him down on
his knees and face fucked him until I filled his mouth with cum.

We cleaned up as best we could and then went back to lie down awhile. I
woke up about 3 hours later at the sound of my cellphone vibrating in my
purse. I quietly dressed then gave Chris a peck on the cheek before heading
back to my room for a nice bubble bath and a gossip fest with the friend I
was supposed to meet the night before. After I got off the phone with him I
got out of the bath, toweled off and crawled into bed for a few hours.

Later that night I went out on the town with my friend and then had some
nice oral interplay with him (all he likes) he dropped me off at the hotel
around 9 at night.  Deciding I wanted a drink before going up to my room I
walked into the bar to see Chris sitting at the same table with a Guinness
and a Midori Sour. I grinned at him as he gave me that still mezmerizing
wry grin and beckoned me over. This girl was going to have another sore ass
in the morning :)

***** Note this is a work of fiction *****

I'd love to spend a weekend enfemme in a hotel room engaging in sexual
escapades but unlike the TV in this story I never engage in bareback
sex. If you're interested in recreating any of this story let me know via
email. I am safe and expect you to be as well. Let me know thoughts,
comments and suggestions on this or any of my other stories.

Lots of Love,
Gabbytv